Berkshire, MA Homes

• 

  

  

  /25

  $335,000

  • 3 Beds
  • 1.5 Baths
  • 1,232 Sq Ft

  182 Church St, Canaan, CT 06018

  Welcome to this classic 3-bedroom Colonial, ideally situated on the outskirts of town yet just a short stroll to the sidewalk district. This home blends timeless charm with functional living spaces, perfect for families or anyone looking for a comfortable setting with easy access to town amenities. Step inside to discover hardwood floors that flow throughout the home, adding warmth and character

  

  Wendy Eichman

  Raynard & Peirce Realty,LLC

  (860) 295-3073

  182 Church St, Canaan, CT 06018
• 

  

  

  /19

  $3,300 per month

  • 1 Bed
  • 1.5 Baths
  • 1,900 Sq Ft
  • House for Rent

  174 Weatogue Rd, Salisbury, CT 06068

  Enjoy a unique retreat at the Lodge! This fully furnished rental boasts a large open floor plan that includes kitchen/dining area, seating area in front of large stone fireplace, sleigh bed, tv area and a beautiful custom bar. One full bath and one half bath. Plenty of space for a gathering or just a few. Vacation at the Lodge and enjoy the beauty of the Northwest Corner of Connecticut.

  

  Wendy Eichman

  Raynard & Peirce Realty,LLC

  (860) 734-4642

  174 Weatogue Rd, Salisbury, CT 06068
• 

  $690,000 Sold Aug 07, 2025

  • 1,080 Sq Ft
  • $639/SF
  • 7 Days On Market

  • 1 Bed
  • 1.5 Baths
  • Built 1985

  28 Rocky Ln, Salisbury, CT 06068

  A rare opportunity awaits on Rocky Lane. This beautifully renovated, energy-efficient one-bedroom cottage offers a serene retreat with deeded Right of Way access to East Twin Lakes. Perfect for swimming, boating, kayaking, or fishing on one of Connecticut's finest managed trout and salmon lakes. The home has been fully updated with newer mechanicals, central air, whole-house generator, and

  Julie Einhorn Compass Connecticut, LLC

  28 Rocky Ln, Salisbury, CT 06068
• 

  

  

  /31

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,160 Sq Ft

  206 E Main St, Ashley Falls, MA 01222

  206 E Main St, Ashley Falls, MA 01222
• 

  

  

  /36

  $899,000

  • 2 Beds
  • 2.5 Baths
  • 1,508 Sq Ft

  48 Preston Ln, Salisbury, CT 06068

  Tucked away on a private road with shared lake access to the serene waters of Lake Washinee, this custom one-level home offers the perfect blend of natural beauty, thoughtful design, and modern comfort. Set on just over three wooded acres with a tranquil stream, the property offers privacy and peaceful surroundings in every direction. The original home was built in 1950. There was a complete

  

  Wendy Eichman

  Raynard & Peirce Realty,LLC

  (860) 792-5920

  48 Preston Ln, Salisbury, CT 06068
• 

  

  /23

  $2,800 per month

  • 3 Beds
  • 1 Bath
  • 1,323 Sq Ft
  • House for Rent

  37 Greene Ave, Canaan, CT 06018

  This desirable fully furnished 3 bedroom rental nestled in a quiet corner of Litchfield County is available this fall September 1, 2025 - June 30, 2026, for an academic rental season. Bright and tastefully decorated, this home is a peaceful retreat offering comfortable country living. This home features a fully equipped spacious kitchen, ideal for entertaining, cozy living and dining areas with

  Roberta Green Elyse Harney Real Estate

  37 Greene Ave, Canaan, CT 06018
• 

  $287,500 Sold Aug 07, 2025

  • 1,368 Sq Ft
  • $210/SF
  • 36 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1930

  58 Barlow St, Canaan, CT 06018

  Charming Colonial with Endless Potential in North Canaan This adorable colonial home is brimming with character and opportunity, offering a solid foundation and room to bring your personal touches. Nestled in a peaceful neighborhood, this home features an open floor plan accented by hardwood and tile floors, creating a warm and inviting living space. The great room boasts cathedral ceilings and a

  Suzie Larson Turning Point Realty, LLC

  58 Barlow St, Canaan, CT 06018
• 

  

  /31

  Est $448,337 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,670 Sq Ft

  166 Berkshire School Rd, Sheffield, MA 01257

  166 Berkshire School Rd, Sheffield, MA 01257
• 

  

  /53

  $695,000

  • 4 Beds
  • 4 Baths
  • 3,455 Sq Ft

  64 Hewins St, Sheffield, MA 01257

  A rare & authentic 1842 post & beam farmhouse w/ many original details. This one-of-a-kind antique home awaits the reinvention & stewardship of it's next owners. In the same family for the last 125 years, and with just two prior owners since being built, the structure features post & beam construction, two original fireplaces, antique hardware, woodwork and doors that exemplify early American

  

  Dan Alden

  ALDEN COUNTRY REAL ESTATE SERVICES

  (413) 296-3500

  64 Hewins St, Sheffield, MA 01257
• 

  

  /23

  $2,400 per month

  • 2 Beds
  • 1 Bath
  • 1,168 Sq Ft
  • House for Rent

  11 Raymond Ave, Canaan, CT 06018

  Located down a quiet country road on the border of North Canaan and Salisbury, this meticulously maintained 2-bedroom Cape is available for annual lease. Pull into the covered carport and enter through the mudroom, complete with generous storage and a dedicated laundry area. The open kitchen offers a new dishwasher, ample space for a dining table, and features large sliding glass doors that lead

  Brierley Hannan William Pitt Sotheby's Int'l

  11 Raymond Ave, Canaan, CT 06018
• 

  

  /37

  $644,000 Sold Aug 01, 2025

  • 1,224 Sq Ft
  • $526/SF
  • 21 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1973

  284 Brewer Branch Rd, Great Barrington, MA 01230

  MID CENTURY MODERN: Built in 1973 of a minimalist design. This very cool home is tucked on a country road. Three bedrooms, two baths with upper level open plan overlooking beautiful light forest. A Fire place anchors the lovely open concept with a wall of windows letting in the sunshine. Perfect as a short term rental when not in use offering guests a beautiful in-ground pool to cool off in the

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  284 Brewer Branch Rd, Great Barrington, MA 01230
• 

  Est $577,311 Not Listed For Sale

  • 7 Beds
  • 2.5 Baths
  • 4,852 Sq Ft

  5 Elm St, Canaan, CT 06018

  5 Elm St, Canaan, CT 06018
• 

  

  /32

  $425,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,700 Sq Ft

  1291 Ashley Falls Rd, Sheffield, MA 01222

  Nestled in the charming village of Ashley Falls, this cozy single-level home offers a perfect blend of comfort and scenic beauty. The open floor plan includes 2 bedrooms, 1 bath, an eat-in kitchen, and a spacious living room with a wood-burning fireplace, large picture windows, and direct access to a screened porch overlooking acres of picturesque farmland. Additional features include a slab

  

  Dan Alden

  ALDEN COUNTRY REAL ESTATE SERVICES

  (413) 728-1649

  1291 Ashley Falls Rd, Sheffield, MA 01222
• 

  

  /14

  $3,700 per month

  • 2 Beds
  • 1 Bath
  • 868 Sq Ft
  • House for Rent

  61 Preston Ln, Salisbury, CT 06068

  Twin Lakes Lakefront Annual Rental Salisbury, CT Furnished Year-Round Rental with direct frontage on Lake Washinee, the smaller and quieter of the Twin Lakes, with a wide lawn and a Dock. $3700. per month starting June 1, 2025 (not by month or season). Features include a Front Deck, Living Room, Dining Area, Kitchen, Sunroom, Mudroom, 2 Bedrooms, 1 Full Bath, Loft, and 1-bay of the Garage. Close

  Juliet Moore Elyse Harney Real Estate

  61 Preston Ln, Salisbury, CT 06068
• 

  $89,250 Sold Jul 31, 2025

  • Land
  • 2.10 Acres
  • $42,500 per Acre

  • 120 Days On Market

  151 Sand Rd, Canaan, CT 06018

  This flat, primarily cleared parcel is three lots that comprise a total of 2.1 acres. It's conveniently located between North Cannan, Falls Village, and Salisbury with a sweet view of Canaan Mountain in the distance. Little to no tree removal is necessary, as much of the lot was once farmland, and active, bountiful corn fields surround the property on two sides. It's just 15 minutes to Great

  David Mallison William Pitt Sotheby's Int'l

  151 Sand Rd, Canaan, CT 06018
• 

  

  /43

  Est $490,508 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,202 Sq Ft

  728 Hewins St, Sheffield, MA 01257

  728 Hewins St, Sheffield, MA 01257
• 

  

  /40

  $499,000

  • 6 Beds
  • 2.5 Baths
  • 3,184 Sq Ft

  119 S Main St, Sheffield, MA 01257

  A unique opportunity to make this terrific property your own, with a separate bungalow apartment for income or other home business uses. Property features a 6 bedroom, 2 bath 1880's Victorian with a classic yet casual style. First floor features a sunny living room, large country kitchen, formal dining room w/ built-ins, and front parlor/bedroom. Second floor offers 5 bedrooms, 2 full baths, and

  

  Dan Alden

  ALDEN COUNTRY REAL ESTATE SERVICES

  (413) 481-1637

  119 S Main St, Sheffield, MA 01257
• 

  

  /15

  $7,000 per month

  • 6 Beds
  • 3 Baths
  • 3,144 Sq Ft
  • House for Rent

  264 Twin Lakes Rd, Salisbury, CT 06068

  Available: May 26, 2025 through September 30, 2025 - Twin Lakes Lodge - Twin Lakes Lodge is a Landmark building located next to O'Hara's Marina. Features of this rental include a primary suite on the first and second floor, living room with a wood burning fireplace and a recently renovated kitchen. Enjoy entertaining or relaxing on the wrap around porch there is also a boat slip available to use

  KATHLEEN DEVANEY Elyse Harney Real Estate

  264 Twin Lakes Rd, Salisbury, CT 06068
• 

  

  /56

  $850,000 Sold Jul 18, 2025

  • 2,430 Sq Ft
  • $350/SF
  • 53 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1979

  812 Canaan Southfield Rd, Southfield, MA 01259

  Spacious, updated and meticulously maintained modernist 4 BR/3 bath escape sits on 4.8 wooded acres, surrounded by mature birch trees and rhododendrons, seasonal creek, and a footbridge to bonus cabin in the woods. Open kitchen (Viking, Bosch)/LR layout featuring a Wittus Shaker wood stove opens to 3-sided raised deck and large screened porch. Two primary bedrooms feature sliding doors to

  Lori Rose STONE HOUSE PROPERTIES, LLC

  812 Canaan Southfield Rd, Southfield, MA 01259
• 

  

  /22

  Est $606,137 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,016 Sq Ft

  169 Ashley Falls Rd, Sheffield, MA 01257

  169 Ashley Falls Rd, Sheffield, MA 01257
• 

  

  /27

  $365,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,733 Sq Ft

  101I Sand Rd, Canaan, CT 06018

  Located in a residential neighborhood on the outskirts of town, this spacious one-level home offers comfortable living with thoughtful updates throughout. The inviting floor plan features hardwood floors, a large living room, formal dining area, and a dedicated office space-perfect for working from home. The remodeled kitchen shines with custom cherry cabinets and ample counter space, ideal for

  

  Wendy Eichman

  Raynard & Peirce Realty,LLC

  (860) 846-4494

  101I Sand Rd, Canaan, CT 06018
• 

  

  /17

  $40,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,326 Sq Ft
  • House for Rent

  23 Ravine Ridge Rd, Salisbury, CT 06068

  Secluded Salisbury Rental With Private Pool & Riverside Charm - Escape to this tranquil 3-bedroom, 2.5-bath cottage nestled at the end of a private road in Salisbury, CT. Thoughtfully furnished and brimming with charm, this home features three fireplaces, rustic brick flooring, and a three-season sunroom perfect for unwinding. Step outside to a riverside patio, where you can sip your morning

  Elyse Morris Elyse Harney Real Estate

  23 Ravine Ridge Rd, Salisbury, CT 06068
• 

  

  /31

  $390,000 Sold Jul 15, 2025

  • 2,008 Sq Ft
  • $194/SF
  • 19 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1804

  95 Main St, Sheffield, MA 01257

  Beautiful Colonial right in the Village Center with acircular driveway and ample parking. Enter to an open kitchen and dining area with exposed beams, gracious living room with walls of windows and a family room with bar, custom stone flooring and fireplace. Convenient access from the family room to the back patio for grilling and entertaining with an exterior fireplace! The 2nd level features

  Cortney Dupont COHEN & WHITE ASSOCIATES

  95 Main St, Sheffield, MA 01257
• 

  

  /13

  Est $464,323 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,330 Sq Ft

  1605 Clayton Mill River Rd, Southfield, MA 01259

  1605 Clayton Mill River Rd, Southfield, MA 01259
• 

  

  /22

  $285,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  339 Alum Hill Rd, Sheffield, MA 01257

  Opportunity awaits the next owners of this privately situated 3 bedroom, 1.5 bath raised ranch. The first floor offers an easy layout of kitchen, laundry room, living room and three bedrooms, one with a private half bath and shared hall full bath. The lower level offers additional unfinished space for expansion and/or storage. The house is ready for updating and will make a great first, second,

  

  Dan Alden

  ALDEN COUNTRY REAL ESTATE SERVICES

  (413) 600-0094

  339 Alum Hill Rd, Sheffield, MA 01257
• 

  

  /35

  $75,000 per month

  • 6 Beds
  • 10 Baths
  • 9,193 Sq Ft
  • House for Rent

  325 Canaan Rd, Salisbury, CT 06068

  Luxurious Estate With Breathtaking Views In Salisbury, Ct - (Availability: $75,000/term: July 2 - September 2, 2025. $40,000/month: July or August to September 1, 2025) Escape to luxury in Salisbury, CT, with this stunning 9,000 sq. ft. estate atop a hill, offering panoramic views of the Housatonic River Valley and the Taconic Mountain Range. This 6-bedroom, 7-full-bath, and 3-half-bath home

  Elyse Morris Elyse Harney Real Estate

  325 Canaan Rd, Salisbury, CT 06068
• 

  

  /40

  $1,250,000 Sold Jul 11, 2025

  • 2,100 Sq Ft
  • $595/SF
  • 12 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1984

  40 Veeley Rd, Sheffield, MA 01257

  A unique example of repurposing executed to perfection. This wonderful Gambrel style home sits on three private acres and used a lot natures offerings to help bring this home to its present glory. The home was built using the beams from a 200 year old barn that once sat on the property. The floors were milled from cherry trees that grew on the parcel, the fireplace stone is from the foundation

  Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

  40 Veeley Rd, Sheffield, MA 01257
• 

  

  /48

  Est $1,592,004 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,800 Sq Ft

  452 Shunpike Rd, Sheffield, MA 01257

  452 Shunpike Rd, Sheffield, MA 01257
• 

  

  /10

  $345,000

  • Land
  • 37 Acres
  • $9,215 per Acre

  0 Old Turnpike Rd N, Canaan, CT 06018

  37.437 acres bordering the Konkapot River. A small portion of this land on the back side is in Massachusetts. New survey is complete. Nice location with great possibilities!

  

  Wendy Eichman

  Raynard & Peirce Realty,LLC

  (860) 609-6471

  0 Old Turnpike Rd N, Canaan, CT 06018
• 

  

  /15

  $13,000 per month

  • 4 Beds
  • 3 Baths
  • 2,167 Sq Ft
  • House for Rent

  Unlisted Address

  Charming Twin Lakes Lakefront Retreat Nestled along the serene shores of Washining Lake, this beautiful 4 bedroom, 3 bath home offers a tranquil retreat for those seeking relaxation and natural beauty. With its spacious interior and breathtaking views, this rental property promises an unforgettable experience. This lake home is the perfect place to create lasting memories. Whether you seek a

  TAMI REID Northwest CT Realty

  Unlisted Address
• 

  $1,300,000 Sold Jun 30, 2025

  • 3,504 Sq Ft
  • $371/SF
  • 22 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 2003

  54 Rocky Ln, Salisbury, CT 06068

  This wonderful Twin lakes retreat is the perfect home for entertaining friends and relatives at all times of year. A short walk across the street leads you to the lovely, deeded lakefront access on Lake Washining, the larger of the two lakes. The home is located off a quiet, private road and set on 1.32 acres. The living room with its vaulted ceiling and wood burning fireplace greats you as you

  David Mallison William Pitt Sotheby's Int'l

  54 Rocky Ln, Salisbury, CT 06068
• 

  

  /36

  Est $377,940 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,379 Sq Ft

  1014 Salisbury Rd, Sheffield, MA 01257

  1014 Salisbury Rd, Sheffield, MA 01257
• 

  

  /35

  $649,000 Under Contract

  • 5 Beds
  • 3 Baths
  • 3,436 Sq Ft

  27 Tobey Hill Rd, Canaan, CT 06018

  Nestled in the foothills of the Berkshires on a quiet country road, this circa 1790 colonial, "The Tobey House," awaits its new stewards! This special property features authentic period details & is sited on a majestic 3.88 acre lot with direct access to the waterfalls at Campbells Falls. The sprawling, versatile floorplan is the perfect canvas to bring your antique Pinterest board to life! With

  Tommy Connors Redfin Corporation

  27 Tobey Hill Rd, Canaan, CT 06018
• 

  

  /59

  $2,295,000 Sold Jun 27, 2025

  • 3,150 Sq Ft
  • $729/SF
  • 1 Day On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1915

  246 County Rd, Sheffield, MA 01257

  Welcome to Brookland, an enchanting property of 23 acres surrounded by the Ironwork Brook. A truly move in ready home, this modern family compound has been gut renovated to the highest standards using custom Danby marble, handmade brass Italian lighting and custom cabinetry. The main house with three bedrooms and two and a half baths has oak flooring throughout, patio access from the main living

  Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

  246 County Rd, Sheffield, MA 01257
• 

  

  /42

  Est $437,893 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft

  505 Sheffield Plain, Sheffield, MA 01257

  505 Sheffield Plain, Sheffield, MA 01257
• 

  

  /9

  $379,500

  • Land
  • 6 Acres
  • $60,720 per Acre

  0 S Main St, Sheffield, MA 01257

  Mountain views with Rt 7 access. Whether you are interested in a private residence to farm, raise horses, or escape the city life or if you are looking for a business opportunity with amazing Rt 7 exposure this land is the perfect opportunity. Totaling 6.25 acres of completely usable, flat, dry land. Currently the fields are hayed and have an approximate 1 acre vineyard. The 6.25 acres is made up

  Grace Golden Equine Homes Real Estate, LLC

  0 S Main St, Sheffield, MA 01257
• 

  $40,000 Sold Jun 23, 2025

  • Land
  • 1.06 Acres
  • $37,736 per Acre

  • 105 Days On Market

  0 Greene Ave Unit 24079621, Canaan, CT 06018

  This is a rare chance to purchase a building lot with the ability to connect to town water. Newly completed survey on this 1.06 acre lot. Located above Route 44 in Greenacres on Greene Avenue with potential access from Ryan Avenue as well. Nice hardwood trees throughout the lot. Inventory is low and this is a great opportunity to build a home of your choice!

  Wendy Eichman Raynard & Peirce Realty,LLC

  0 Greene Ave Unit 24079621, Canaan, CT 06018
• 

  

  /56

  Est $1,147,919 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,929 Sq Ft

  49 Bow Wow Rd, Sheffield, MA 01257

  49 Bow Wow Rd, Sheffield, MA 01257
• 

  

  /40

  $999,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,878 Sq Ft

  1166 Rannapo Rd, Sheffield, MA 01257

  It's no wonder why this property is the home of Berkshire county's oldest elm tree! The abundant sunshine, quietude and peace would make anybody want to set down roots and stay a while. This light filled home has refinished wood floors throughout the main level. Kitchen has granite counters, ample cabinet space, pantry and large island. As part of the open floor plan there is a bright dining room

  Grace Golden Equine Homes Real Estate, LLC

  1166 Rannapo Rd, Sheffield, MA 01257
• 

  

  /34

  $795,000 Sold Jun 09, 2025

  • 2,633 Sq Ft
  • $302/SF
  • 12 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1949

  371 Berkshire School Rd, Sheffield, MA 01257

  Step into a world of elegance and comfort with this gracious home, bathed in natural light and designed for sophisticated living. Set on a sprawling three-acre lot, this property features well-designed rooms that create an inviting atmosphere for both relaxation and entertainment. At the heart of the home, the updated kitchen serves as a culinary haven. The first-floor primary en-suite bedroom

  Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  371 Berkshire School Rd, Sheffield, MA 01257

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